Lithium borohydride → HCID 69672974, compound

HRID 1751719Notes

Reaction equation

HRID 1751719 reaction equation
[C:1]([O:5][C:6]([N:8]1[C@@H:12]([C:13](OC)=[O:14])[CH2:11][CH2:10][C@H:9]1[C:17]([OH:19])=[O:18])=[O:7])([CH3:4])([CH3:3])[CH3:2].[BH4-].[Li+]>C(OCC)C.CO>[C:1]([O:5][C:6]([N:8]1[C@@H:12]([CH2:13][OH:14])[CH2:11][CH2:10][C@H:9]1[C:17]([OH:19])=[O:18])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 4148881Lithium borohydrideHCID 69672805HCID 69672805, compound

Product 1

HCID 69672974HCID 69672974, compoundYield 88.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
70 °C

Procedure

To an ice cold solution of (2S,5R)-1-(tert-butoxycarbonyl)-5-(methoxycarbonyl)pyrrolidine-2-carboxylic acid (1.17 g, 4.07 mmol) in 70 mL diethyl ether and 0.330 mL methanol was added lithium borohydride (2M in THF, 4.0 mL, 8.14 mmol). After 10 minutes, the ice bath was removed and the reaction was heated at reflux overnight. As the reaction had not proceeded, a solvent swap to THF was performed, and the resulting mixture was heated at 70° C. overnight. The reaction mixture was cooled to 0° C. and quenched with 1N HCl and then extracted into ethyl acetate, dried over sodium sulphate, filtered and concentrated under reduced pressure to give the crude product as a white semi-solid (886 mg)

Workup

  1. customthe ice bath was removed
  2. temperaturethe reaction was heated
  3. temperatureat reflux overnight
  4. temperatureThe reaction mixture was cooled to 0° C.
  5. customquenched with 1N HCl
  6. extractionextracted into ethyl acetate
  7. dry with materialdried over sodium sulphate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-acb6e8a35c7c4bd3a33782bd7ced7191
Source dataset
uspto-grants-2015_10
Patent number
US09156823B2

Reaction notes

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